Process for the production of new azo dyestuffs insoluble in water



1 wherein R means an aryl residue,

Patented 0a. 27, 1925,

UNITED STATES PATENT OFFICE,

GEQRG KALISCHER, 0F MZAINKUR, NEAR FRANKFORT-ON-THE-MAIN, AND KARIJ KELLER, 0F FRANKFORT-ON-THEMAIN, GERMANY, ASSIGNORS TO LEOYOLD CASSELLA &: G0,, GESELLSCI-IAFT UL? GERMANY.

rnoonss non arms: rnonuorron No Drawing.

German Re ublic, residing at Frankfort-on ermany, have invented a Procthe-Main,

wherein R means an aryl residue, X an azo group or an azoxy group N-N-Ar i Application filed March 24, 1825. serial No. 18,054.

droxynaphthoic acid, having the BET BESCHRKNKTER HAFTUNG, A CORPORATION OF NEW AZO DYESTUFFS INSOLUBLE IN WATER.

ess for the Production stufi's Insoluble in Water, which may boobtained by combining an diazo c mpoundwith a derivative of the arylides 0 2.3-hyformula The new dyestufi's having probably the general formula:

X an azo are, when dry, orange to black powders, dissolving in sulfuric acid with agreen to violet color and yielding upon reduction with stannous chloride two molecules of an aromatic amine and of" an aminoarylide of 1-an1ino-2- hydroxy-naphthalene-3-carboxy1ic acid of the general formula:

The process of producing the final dyestufis may he carried out in an excellent way on the fibre, owing to the fact that the arylides' containing the szo or ezoxy group according to the above described formula show naphthoic acid.

The invention is illustrated by the -follo'wg exampl Ewample. 4 I g 0, p rts of the product, obtained of l lew Azo Dvegeneral remarkable inte'nor by a agents in an alkaline solution to act on mtroarylides of 2.3 hydroxy duemg in alkaline solution 1 meta-nitm ortho-toluidide acid, ofthe formula;

of 2.3-hydroxynaphthoie; a

tion, made up with parts, 10 parts of Well Wetteol cotton are en- 'rubbing and washing is remarkable.

- either not substituted are dissolved with 0.8 part-0f caustic soda solution of 40 Be. in hot water by adding a little Turkey-re'cl-oil. Into the boiling soluhot Water to about 200 tered and. dyed for about an. hour in the N N 0 Ha cooling bath. It is then rinsed with cold water and whizzed. The subsequent development takes place in the usual manner with a diazo solution of mete-nitroperetoluidine,

yielding on the fibre an axe dyestufi of the following formula:

only by a greater or smaller llifierence of shade from those, obtained according to the example. In this manner for instance, by using the product of reduction of the mete.- nitraiiilide of 2.3-hydroxynaphthoic acid and diazotized metenitraniline, a yellowish or- -ange, by using diezotized pere-nitro-oithotoluidine abluish red, by using aminoezotoluene at claret, by using tetrazotizecl yo-d;- snisidine a blue dyeing results, the clyestufi formed on the fibre having probably the :tol-= lowing formula:

OOH:

3 Q.H-..l

By using the product of reduction of the para-nitranilitle of 2.3lly(lroxynaphthoic acid similar shades are obtained.

Having now particularly described and. ascertained the nature of our said invention and in what manner the same is to be performed, We declare, that what We clein'i is:

1. As new'compounds the 2120 dyestufis, insoluble in Water, having probably the general formula:

Aryl-N N wherein R means an aryl residue, X an azo group or an azoxy group which when dry are orange to black powders, dissolving in sulfuric acid with a green to violet colorand yielding upon reduction with stannous chloride two molecules of an aromatic amine and an aminoarylide of l-amino-Q hydrox naphthalene-3-carboxylic acid of the general formula:

the arylides of 2.3-hydroxynaphthoic acid, having the general formula;

wherein R means an aryl residue, X aneazo group i N=N or an azoxy group 3. Materials dyed with the 'new azo dyestuffs of claim 1, said dyestuffs being developed on the fibre of the materlal.

In witness whereof they have hereunto signed their names this eleventh day of March, 1925.

GEOBG KALISCHER. KARL KELLER. 

